1. Field Of The Invention
This invention relates to a poly(N-cyclic iminoether), processes for production thereof, a thermosetting composition containing it, and a thermoset resin.
C-cyclic iminoether compounds, such as C-oxazoline and C-oxazine compounds, have previously been known, and used, for example, for modification of polyesters by reducing the amount of a terminal carboxylic acid or for improving polymer properties by chain extension. They are also used as materials for production of thermosetting resins by reaction with carboxylic acids, aromatic alcohol or aromatic amines.
2. Description Of The Prior Art
Japanese Laid-Open Patent Publications Nos. 40681/1988 and 26628/1989 disclose processes for producing a thermoset resin by heating (A) a poly(C-cyclic iminoether) having 2 to 4 cyclic iminoether groups in the molecule, (B) a polyepoxy compound and (C) a polyamine, an intramolecular acid anhydride and an aromatic polyhydroxy compound in the presence of an acid catalyst.
Japanese Laid-Open Patent Publication No. 33119/1989 discloses an epoxy curing agent comprising 0.05 to 0.2 mole of a C-oxazoline of the following formula ##STR1## wherein
X represents a divalent organic group,
D represents a divalent organic group and n is 0 or 1,
and 1 mole of an acid anhydride.
Japanese Laid-Open Patent Publication No. 104838/1987 discloses a process for producing a thermoset resin by reacting a 2,2'-(1,3-phenylene)bis(2-oxazoline) derivative with a compound selected from polycarboxylic acids, polyhydric alcohols and polyamines.
Japanese Laid-Open Patent Publication No. 75024/1988 discloses a thermosetting resin composition comprising (A) an epoxy compound, (B) a C-oxazoline compound, (C) a curing agent, for example a compound having a carboxyl, hydroxyl, acid anhydride or sulfonic group or an organosilane or organosiloxy compound, and as required, (D) a granular or fibrous filler.
U.S. Pat. No. 4,628,102 discloses the production of a compound containing both bicyclic amide acetal and epoxy functional groups by reacting a diepoxide compound and a mono(C-oxazoline).
U.S. Pat. No. 4,652,620 discloses the production of substantially insoluble and infusible crosslinked resinous compositions by reacting a mixture of a multifunctional epoxide, a phenolic compound and a compound containing at least two C-oxazoline groups in the melt phase.
Japanese Laid-Open Patent Publication No. 26627/1989 discloses the production of a thermoset resin by the reaction of a polyepoxide compound with a C-cyclic iminoether such as a C-oxazine or C-oxazoline.
Japanese Laid-Open Patent Publication No. 1533/1984 discloses a process for producing a thermoset resin which comprises reacting bis(C-oxazoline) compound and not more than 1 mole, per mole of the C-oxazoline compound, of a dicarboxylic acid under heat in the presence of a phosphite ester.
Japanese Laid-Open Patent Publication No. 146924/1988 discloses a process for producing a poly(etheramide) which comprises copolymerizing C-oxazoline and a bis- or poly-phenolic compound in the presence of an alkali or alkaline earth metal cation complex (catalyst) at a temperature of 100.degree. to 200.degree. C.
Japanese Patent Publication No. 57330/1986 discloses a process for producing a C-oxazoline-modified unsaturated polyester which comprises reacting a C-oxazoline derivative having 1 to 4 oxazoline rings in the molecule with an unsaturated polyester having carboxyl groups. This publication states that the reaction is carried out at a temperature of 100.degree. to 250.degree. C. for about 10 minutes to 3 hours.
Japanese Laid-Open Patent Publication No. 48811/1989 discloses a thermosetting unsaturated polyester composition comprising an organic compound having a C-oxazoline ring and a boiling point of at least 140.degree. C., an unsaturated polyester resin, reinforcing fibers such as glass fibers and a polymerization initiator (peroxide).
U.S. Pat. No. 4,551,511 discloses a process for preparing anhydride/styrene copolymers of higher molecular weight comprising heating a mixture of maleic anhydride, styrene and a small amount of C-oxazoline at a temperature in the range of from 50.degree. C. to 150.degree. C.
U.S. Pat. No. 4,351,936 discloses a process for producing a saturated polyester having a reduced terminal carboxyl group content, which comprises reacting a carboxyl-terminated saturated polyester with a monocyclic iminoether compound. The specification of this patent describes a mono N-, O- or C(0)-cyclic iminoether compound as the monocyclic iminoether compound.